Painting a shoe sole portion has traditionally been a labor-intensive process that requires a human operator to manually tape or mask all the areas of the shoe sole portion that are not to be painted. The human operator then manually paints any portions of the shoe sole portion that are left exposed. Replacing the manual painting process with an automated painting system has been challenging not only due to the difficulty in constructing a universal jig that is able to secure the shoe sole portion in such a way that only a paintable surface is left exposed but also due to difficulties in constructing the jig so that it is able to secure a wide variety of styles and sizes of shoe sole portions. Additionally, it has been challenging to automate the opening of the jig after the shoe sole portion has been painted and to automate the removal of the painted shoe sole portion from the open jig.